Hi,
Just do the check again on a fresh Windows VM (to avoid path or deps trouble) and all work fines with apachelounge httpd distrib.
more *.so | grep -a libssl well return libssl-1_1-x64.dll
@DnvrSysEngr are you using « -avx » release or standard (SSE2) one?
If AVX, is the return of coreinfo | grep -i avx a - or a * ?

So, I now understand what appends after your precision on DEPS libcurl.
I tested Apachelounge release keeping my production path including my httpd release bin path in - including all my own build dll deps...
I build libcurl with libcurl-vc15-x64-release-dll-cares-dll-zlib-dll-ipv6-sspi-winssl-nghttp2-dll <= understand that you must have c-ares, nghttp2 and zlib dll in your path (dynamic link)